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Hillsborough County, FL vacation rentals
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Best Vacation rentals and Airbnb offers in Hillsborough County, FL

Best family friendly Hillsborough County, FL vacation rentals

Among the 33226 accommodations in Hillsborough County, FL, here are the 4 best family friendly rentals

Apartment W/ Easy Access To Indian Rocks Beach! - Hillsborough County, FL
9.7 194 reviews

Apartment W/ Easy Access To Indian Rocks Beach!

apartment, Indian Rocks Beach
This one-bedroom apartment is a short walk from Indian Rocks Beach and is close to Indian Shores Beach, offering easy access to the beautiful Florida coastline. Guests rave about the apartment's excellent location, cleanliness, and overall experience.
The 450-square-foot apartment comfortably accommodates up to four guests and includes a fully equipped kitchen, a washing machine, and a private Jacuzzi. Enjoy amenities like a garden, spa, and tennis court, all while staying connected with free Wi-Fi and cable TV.
Remodeled 2/2 King Bed Pool And Grill, 5min> Beach - Hillsborough County, FL
9.6 125 reviews

Remodeled 2/2 King Bed Pool And Grill, 5min> Beach

apartment, Largo
This contemporary condo is located in Largo, Florida, just minutes from Indian Rock Beach, Publix, Largo Mall, and a golf course. The apartment has received excellent ratings for location, cleanliness, and user experience.
The two-bedroom, two-bathroom apartment offers 1000 square feet of space and can comfortably accommodate up to six guests. Amenities include a fully equipped kitchen, air conditioning, a washer and dryer, a patio, access to a swimming pool, fitness center, and free parking.
Land's End 1-301 Gulf View - Premier - Hillsborough County, FL
9.6 61 reviews

Land's End 1-301 Gulf View - Premier

house, Treasure Island
This charming beach house is located just steps from Sunset Beach and a short walk to Treasure Island's main attractions, making it the perfect spot for exploring the area. The house has consistently received excellent reviews for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The 800-square-foot house can accommodate up to 2 guests in its one bedroom and one bathroom. Enjoy the fully equipped kitchen, air conditioning, swimming pool, jacuzzi, terrace, garden, fitness center, tennis court, and free parking, all while being just steps away from the beach.
Newly Renovated  10 Mins To Beaches  Firepit - Hillsborough County, FL
10 212 reviews

Newly Renovated 10 Mins To Beaches Firepit

house, Bardmoor
This Bardmoor vacation rental is centrally located in Pinellas County, Florida, within a few miles of Lake Seminole Park and the Pinellas Trail, and 5-15 miles from beaches like Clearwater Beach and St. Pete Beach.
This newly renovated 3-bedroom, 2-bathroom home offers 1,110 square feet of space, sleeps six guests, includes a fenced backyard with a firepit and grill, and provides amenities like a pack 'n play and high chairs for families.

Top cities

Best Hillsborough County, FL vacation rentals with a pool

Among the 33226 accommodations in Hillsborough County, FL, here are the 4 best rentals with a pool

Picturesque Waterfront Condo View Of Tampa Bay - Hillsborough County, FL
9.9 44 reviews

Picturesque Waterfront Condo View Of Tampa Bay

apartment, Tampa
This waterfront condo is located near Tampa International Airport (TPA) and within walking distance of public beaches, dining options, and the Courtney Campbell trail.
This one-bedroom, one-bathroom unit accommodates up to four guests and features a fully equipped kitchen, air conditioning, a swimming pool, garden, and parking, with coin-operated laundry facilities available on the third floor.
Pool View In A Modern Condo - Feel At Home - Hillsborough County, FL
9.9 226 reviews

Pool View In A Modern Condo - Feel At Home

apartment, Clearwater
This family-friendly Clearwater condo is located within a 3km radius of Morton Plant Hospital, Clearwater Country Club, and the Church of Scientology. It has excellent user, location, and cleanliness ratings. The apartment has one bedroom, one bathroom, and can accommodate up to four guests in a 730-square-foot space. Amenities include a private pool, a fitness center, a garden, a terrace, a spa, a fully-equipped kitchen, and a Smart TV with a DVD player.
Amazing Main Floor Condo At Avalon - Hillsborough County, FL
9.8 166 reviews

Amazing Main Floor Condo At Avalon

apartment, Clearwater
This Clearwater apartment is conveniently located within walking distance of medical facilities, the Church of Scientology, and Clearwater Country Club, offering easy access to both local attractions and healthcare. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience.
This one-bedroom apartment comfortably sleeps three guests and offers 730 square feet of living space. Amenities include a private pool, a fully equipped kitchen, a fitness center, and a washer and dryer, ensuring a comfortable and convenient stay.
Sunny Side Cottages - Hillsborough County, FL
8.5 531 reviews

Sunny Side Cottages

apartment, Dunedin
Sunny Side Cottages is located in Dunedin, Florida, just a short drive from Caladesi Island State Park Beach and other popular attractions. The property consistently receives excellent ratings for cleanliness, location, and overall user experience.
The apartment features one bedroom and one bathroom, providing comfortable accommodations for travelers. Guests can enjoy amenities such as a swimming pool, jacuzzi, garden, and free Wi-Fi, ensuring a relaxing and enjoyable stay.

Frequently Asked Questions about vacation rentals in Hillsborough County, FL

  • What are the must-see sights in Hillsborough County, Florida?

    For must-see sights in Hillsborough County, you've got plenty of options! The Florida Aquarium is a fantastic place to spend the day, especially if traveling with kids. Busch Gardens Tampa Bay offers thrilling rides and animal encounters. Ybor City, Tampa's historic Cuban district, is a must-see for its architecture, cigar shops, and vibrant nightlife. Then there's the Henry B. Plant Museum, housed in a stunning Victorian hotel, and the Tampa Riverwalk, perfect for a stroll.
  • What are the best Airbnb and vacation rentals in Hillsborough County, FL?

    Private Apartment Near The Airport, Davis Islands Gem: Cozy/quiet And Pet Friendly and 303 - New Listing Waterfront - Heated Pool 2 Min To Airport are the most popular Airbnb and vacation rentals in Hillsborough County, FL among travelers.

  • Are there unique natural phenomena in Hillsborough County, Florida?

    While Hillsborough County doesn't have, say, geysers, its unique natural beauty lies in its diverse ecosystems. The beaches along the Gulf Coast offer stunning sunsets and opportunities for shelling. Hillsborough River State Park provides hiking trails and glimpses of Florida's natural landscape, including diverse birdlife. Exploring the many parks and preserves reveals the area's rich biodiversity.
  • What are the most popular Airbnbs in Hillsborough County, FL?

  • What essentials should you bring along for a trip to Hillsborough County, Florida?

    Pack light, breathable clothing suitable for warm, humid weather. Sunscreen, sunglasses, and a hat are absolute necessities, especially during peak sun hours. Comfortable walking shoes are a must, given the amount of walking you'll likely do. Don't forget insect repellent, especially if you plan on spending time outdoors, and a reusable water bottle to stay hydrated.
  • What are the best vacation rentals with a pool in Hillsborough County, FL?

  • What famous events or festivals are happening in Hillsborough County, Florida?

    Hillsborough County hosts many events throughout the year. The Gasparilla Pirate Festival is a huge, well-known event featuring a parade and a pirate invasion. The Florida State Fair is another popular annual event with rides, food, and entertainment. Check local listings for smaller, neighborhood festivals and events happening during your visit.
  • What are the best rentals for families and kids in Hillsborough County, FL?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Hillsborough County, Florida?

    A daily budget will vary greatly depending on your travel style. For a mid-range budget, you could plan on $150-$300 per day. This covers a moderate hotel, meals at a mix of restaurants and cafes, local transportation like ride-sharing or public transit, and entry fees to attractions. Luxury travel will obviously be significantly more expensive.
  • What are the best rentals or Airbnbs with a jacuzzi in Hillsborough County, FL?

  • Where can you find the best restaurants serving local dishes in Hillsborough County, Florida, and what are the must-try specialties?

    For authentic Cuban cuisine, head to Ybor City. Columbia Restaurant is a historic landmark serving traditional dishes. Bern's Steak House is a Tampa institution known for its exceptional steaks and extensive wine cellar. Many restaurants along the Riverwalk offer fresh seafood. You should definitely try Cuban sandwiches, fresh seafood, and key lime pie.
  • What are some less-famous attractions in Hillsborough County, Florida that are worth a visit?

    The Tampa Bay History Center offers a fascinating look at the area's past. The Glazer Children's Museum is a great option for families. The University of Tampa campus is architecturally beautiful and worth a wander. Check out smaller, local museums and art galleries for a more unique experience.
  • What are the best activities for engaging with locals and understanding their culture in Hillsborough County, Florida?

    Visiting local farmers' markets allows you to interact with vendors and sample local produce. Attending a community event or festival provides a chance to mingle with residents. Exploring Ybor City and engaging with the local businesses and residents can offer insight into the area's rich Cuban heritage. Simply striking up conversations with people you meet shows genuine interest.
  • What unique natural landscapes and terrain features can travelers explore in Hillsborough County, Florida?

    Hillsborough County boasts a variety of landscapes. The beaches along the Gulf Coast offer sandy shores and calm waters. Hillsborough River State Park features diverse flora and fauna, including cypress swamps and hardwood forests. Exploring the various parks and preserves reveals the county's natural beauty, from coastal areas to inland wetlands.
  • How many days are ideal for visiting Hillsborough County, Florida, and what are some itinerary suggestions?

    Three to five days is a good amount of time to experience Hillsborough County. A possible itinerary could include one day for the Florida Aquarium and Riverwalk, one day for Busch Gardens, and one day exploring Ybor City and the historic districts. You could add a day trip to a beach or state park, depending on your interests.

Nearby regions

Best Hillsborough County, FL vacation rentals with a balcony

508 Bayshores Yacht Tennis Club - Hillsborough County, FL
9.1 75 reviews

508 Bayshores Yacht Tennis Club

house, Indian Shores
508 Bayshores Yacht & Tennis Club is a 5-minute walk from Indian Shores Beach in Clearwater Beach. It has very good user and cleanliness ratings, and an excellent location rating.
This 1100 square foot air-conditioned vacation home has a spacious seating area, a fully equipped kitchen, satellite TV, a private bathroom, and free Wi-Fi. Guests have access to the pool and tennis courts at the Bayshores Yacht & Tennis Club.
Amazing Beachside Studio - Hillsborough County, FL
9.3 168 reviews

Amazing Beachside Studio

apartment, St. Pete Beach
This St. Pete Beach apartment is located just steps from Upham Beach Park and a short walk from the vibrant Corey Ave, where you'll find shops, restaurants, and bars. The apartment boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The one-bedroom, one-bathroom apartment provides 500 square feet of space and can comfortably accommodate up to four guests. Enjoy amenities like a swimming pool, jacuzzi, and a fully equipped kitchen, along with a terrace, garden, and spa for relaxation.
Wine-dine-sunshine Cozy Flat In The Heart Of Dtsp - Hillsborough County, FL
9.9 265 reviews

Wine-dine-sunshine Cozy Flat In The Heart Of Dtsp

house, St. Petersburg
This studio apartment is located in Downtown St. Petersburg, just a short walk from the waterfront, marina, and St. Pete Pier. It has received excellent ratings for location, cleanliness, and user experience.
The studio, with its 370 square feet, comfortably accommodates up to 3 guests and features a well-equipped kitchen, a luxurious jacuzzi tub, a private balcony, and access to a swimming pool, spa, and concierge services.
Luxurious Waterfront Condo! Great Reviews! - Hillsborough County, FL
10 53 reviews

Luxurious Waterfront Condo! Great Reviews!

apartment, St. Petersburg
This Isla del Sol golf condo rental is ideally situated in St. Petersburg, Florida, within three miles of St. Pete Beach and Pass-a-Grille Beach.
This two-bedroom, two-bathroom unit boasts a fully equipped kitchen, private balcony, access to a swimming pool, jacuzzi, and on-site water park, plus free Wi-Fi and parking.

Neighborhoods and points of interest in Hillsborough County, FL

Best Hillsborough County, FL vacation rentals with parking

Caffeinated Bungalito Near Armature Works|75in Tv - Hillsborough County, FL
9.9 226 reviews

Caffeinated Bungalito Near Armature Works|75in Tv

house, Tampa
This Tampa guesthouse, located near Armature Works (0.6 miles), Ybor City (2.2 miles), Amalie Arena, and Raymond James Stadium (2.5 miles), offers easy access to major attractions.
The 600-square-foot property features a queen bed, queen sofa bed, two TVs (75-inch and 55-inch), a fully equipped kitchen with modern appliances, a large bathroom with a walk-in shower and washer/dryer, and accommodates up to four guests.
New - Paradise At Clearwater - Fabulous Vacation - Hillsborough County, FL
9.6 122 reviews

New - Paradise At Clearwater - Fabulous Vacation

apartment, Clearwater
This Clearwater apartment is conveniently located near Wright Park and Morton Plant Hospital, making it a great option for those seeking medical care or visiting loved ones. It consistently receives excellent ratings for location, cleanliness, and overall experience.
The one-bedroom apartment offers 760 square feet of space and can comfortably accommodate up to four guests. Enjoy a range of amenities, including a swimming pool, fitness center, spa, and a fully equipped kitchen, allowing you to relax and enjoy your stay in Clearwater.
Luxury 1 Bdrm, Relaxing, Coastal Style Condo - Hillsborough County, FL
9.8 88 reviews

Luxury 1 Bdrm, Relaxing, Coastal Style Condo

apartment, Clearwater
This Clearwater apartment is conveniently located within walking distance of Wright Park, Morton Plant Hospital, and Pinellas County Primary Care and Hospitalists, and within a short drive of the Church of Scientology and Clearwater Country Club. Guests have consistently rated this property excellent for location, cleanliness, and overall experience.
The apartment offers a comfortable 730 square feet of living space with one bedroom and one bathroom. Enjoy amenities like a private pool, fitness center, garden, and a kitchen equipped with a fridge, microwave, and dishwasher, perfect for a relaxing and enjoyable stay.
Relaxing Avalon Condo W/heated Pool, Min. To Beach - Hillsborough County, FL
10 51 reviews

Relaxing Avalon Condo W/heated Pool, Min. To Beach

apartment, Clearwater
This Clearwater Beach apartment rental is centrally located, a 10-minute drive from Clearwater Beach and a 15-minute drive from Sand Key Park.
The one-bedroom, one-bathroom condo sleeps three, features a California king bed, full kitchen with dishwasher, and offers access to a swimming pool, fitness center, and parking; note that there are 18 steps to access the unit.
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